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Levocarnitine compound and new preparation method thereof

A synthesis method and catalyst technology, applied in the field of levocarnitine compound and its new method, can solve the problems of cumbersome steps, low yield, expensive, etc.

Inactive Publication Date: 2010-11-03
HAINAN MEILAN SMITH KLINE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reactions of these methods are relatively complicated and the steps are cumbersome, resulting in low final yields, which cannot meet industrial production, and many reaction highly toxic reagents, sodium cyanide and mercuric chloride, and the chiral catalysts used for catalytic reduction are ruthenium and optically active pyridine. Phosphorous ligand complexes are relatively expensive

Method used

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  • Levocarnitine compound and new preparation method thereof
  • Levocarnitine compound and new preparation method thereof
  • Levocarnitine compound and new preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0037] The synthesis of embodiment 1 (R)-4-chloro-3-hydroxyl-butyric acid ethyl ester

[0038] Dissolve 165g (1mol) of ethyl 4-chloroacetoacetate in 300ml of ethanol, add it to the hydrogenation reactor, and then add 10g of L-tartaric acid to modify Ni-B / SiO 2 Catalyst, close the reactor, replace the air in the reactor with nitrogen, then replace the nitrogen with hydrogen, keep the pressure of the reactor at 10kg, then increase the temperature and control it at 60°C, react for 5 hours, leave it to cool, and concentrate the reaction mixture under reduced pressure , the concentrate was distilled under high vacuum, and the fraction at 70° C. (about 0.5 mmHg) was collected to obtain 155 g of (R)-4-chloro-3-hydroxyl-butyric acid ethyl ester, a colorless transparent liquid. The yield: 93%, and the optical purity was 98%.

Embodiment 2

[0039] The synthesis of embodiment 2 levocarnitine

[0040]Dissolve 24g (0.6mol) of sodium hydroxide in 600ml of 10% (1mol) trimethylamine aqueous solution, and slowly add dropwise to 84g (0.5mol) (R)-4-chloro-3-hydroxyl at 0-5°C - Dissolve ethyl butyrate in a solution formed by 1000ml of chloroform, control the drop rate at 4-6ml / min, continue to stir and react at 0-5°C for 15 hours, then gradually rise to room temperature, react for 24 hours, and remove by layers For the organic phase, concentrate the aqueous phase, stir and add Ambertlite IR-120 resin, absorb for 30 minutes, wash the resin three times with depurified water, and then wash the product three times with 10% ammonia water, combine the ammonia solution, concentrate, and obtain a white solid levocarni Tin product 68.1g, yield 84.1%, [α] 20 =-29.5° (c=1, H 2 O).

Embodiment 3

[0041] The synthesis of embodiment 3 (R)-4-chloro-3-hydroxyl-butyric acid ethyl ester

[0042] Dissolve 165g (1mol) of ethyl 4-chloroacetoacetate in 300ml of ethanol, add it to the hydrogenation reactor, and then add 10g of L-tartaric acid to modify Ni-B / SiO 2 Catalyst, close the reactor, replace the air in the reactor with nitrogen, then replace the nitrogen with hydrogen, keep the pressure of the reactor at 12kg, then increase the temperature and control the reaction at 50°C, react for 6 hours, leave it to cool, and concentrate the reaction mixture under reduced pressure , the concentrate was distilled under high vacuum, and the fraction at 70°C (about 0.5mmHg) was collected to obtain 157.5g of (R)-4-chloro-3-hydroxy-butyric acid ethyl ester, a colorless transparent liquid, yield: 94.5%, optical purity 97%.

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Abstract

The invention relates to a levocarnitine compound and a new preparation method thereof. 4-chloracetyl ethyl acetate serving as an initiative raw material is reacted with trimethylamine to generate the levocarnitine compound by using L-tartaric acid modified Ni-B / SiO2 as a catalyst in the presence of sodium hydroxide. The new preparation method has simple reaction steps, obviously lowers the cost and is more suitable for industrialized production.

Description

technical field [0001] The invention relates to a levocarnitine compound and a new method thereof, belonging to the technical field of medicine. Background technique [0002] Levocarnitine, also known as L-carnitine, chemical name: (R)-3-carboxy-2-hydroxy-N,N,N-trimethyl-1-propylammonium hydroxide, internal salt, molecular formula: C 7 h 15 NO 3 , molecular weight: 161.20, structural formula: [0003] [0004] L-carnitine is a special amino acid that widely exists in human body tissues. It is an essential nutrient for humans and animals. It is a vitamin-like nutrient, which is equivalent to vitamin B family. Studies have found that L-carnitine is a compound related to fatty acid metabolism in animals, and its basic function is to assist long-chain fatty acids to penetrate the mitochondrial inner membrane for β-oxidation. Levocarnitine is an essential nutrient whose function is closely related to the metabolism of living organs and tissues. It has also been found tha...

Claims

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Application Information

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IPC IPC(8): C07C229/22C07C227/08
Inventor 胡建荣
Owner HAINAN MEILAN SMITH KLINE PHARMA
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